US5374301A - Inks suitable for use in ink jet printing - Google Patents
Inks suitable for use in ink jet printing Download PDFInfo
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- US5374301A US5374301A US07/983,170 US98317092A US5374301A US 5374301 A US5374301 A US 5374301A US 98317092 A US98317092 A US 98317092A US 5374301 A US5374301 A US 5374301A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
Definitions
- This invention relates to inks, particularly inks containing volatile amine salts of azo compounds which are useful in ink jet printing.
- an ink comprising a liquid medium and a compound of Formula (1) or salt thereof: ##STR2## wherein: Ar and Ar 1 are each independently aryl or substituted aryl providing at least one of Ar and Ar 1 has at least one substituent selected from COOH and COSH;
- J and J 1 are each independently of formula (2), (3) or (4): ##STR3## each R 5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR 6 ;
- R 6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl;
- each T is independently alkyl
- each W is independently selected from H, CN, CONR 10 R 11 , pyridinium and COOH;
- each m is an alkylene chain having 2 to 8 carbon atoms
- B is H, alkyl or COOH
- R 1 , R 2 , R 3 , R 4 , R 10 and R 11 are each independently H, alkyl or substituted alkyl;
- L is a divalent organic linking group
- n 0 or 1
- each X is independently carbonyl or a group of the Formula (5), (6) or (7): ##STR4##
- Z is OR 7 , SR 7 or NR 8 R 9 ;
- Y is H, Cl , CN or Z;
- E is Cl or CN
- R 7 , R 8 and R 9 are independently H, alkenyl, substituted alkenyl, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring; provided (i) if the compound of
- Formula (1) has no --SO 3 H groups then it has at least two groups selected from --COOH and --COSH; and (ii) the compound of Formula (1) has at least as many groups selected from --COOH and --COSH as --SO 3 H groups.
- the compound of Formula (1) has at least as many --COOH as --SO 3 H groups.
- the compound of Formula (1) preferably has at least two and more preferably at least three --COOH groups.
- Ar--N ⁇ N--J and Ar--N ⁇ N--J 1 are such that the compounds of Formula (1) are yellow. It is also preferred that compounds of Formula (1) are free from cellulose reactive groups.
- the groups Ar and Ar 1 are preferably independently selected from naphthyl, substituted naphthyl, phenyl and substituted phenyl, especially phenyl and substituted phenyl.
- the optional substituents on Ar and Ar 1 are preferably selected from alkyl, especially C 1-4 -alkyl; substituted C 1-4 -alkyl; alkoxy, especially C 1-4 -alkoxy; --SO 3 H; --PO 3 H 2 ; --COSH; --OH; --CO 2 H; halogen, especially Cl or Br.
- Ar and Ar 1 are substituted the substituents are independently selected from CO 2 H, COSH and SO 3 H, especially CO 2 H.
- at least one of Ar and Ar 1 has at least one --COOH substituent but it is even more preferred that each of Ar and Ar 1 has at least one --COOH substituent and more particularly at least two --COOH substituents as in, for example, dicarboxyphenyl.
- Each R 5 is preferably independently selected from H, C 1-4 -alkyl, substituted C 1-4 -alkyl, C 1-4 -alkoxy, Cl, CN, Br, ureido or NHCOR 6 , more preferably H, C 1-4 -alkyl, C 1-4 -alkoxy, ureido or NHCO(C 1-4 -alkyl), especially H, methyl, methoxy or ureido.
- Each R 5 is preferably ortho with respect to the azo group connected to the same ring.
- R 6 is preferably H, C 1-4 -alkyl, phenyl or (CH 2 ) 1-4 -phenyl, all of which are either unsubstituted or substituted. R 6 is more preferably C 1-4 -alkyl.
- Each T is preferably independently C 1-6 -alkyl, especially C 1-4 -alkyl.
- the group (m) present in Formula (3) is branched chain alkylene or preferably straight chain alkylene.
- B is preferably H.
- X is of Formula (6) it is preferred that Z is attached to the carbon atom between the two ring nitrogen atoms and that Y is para with respect to Z.
- Each X independently is preferably of Formula (5).
- Z is preferably NR 8 R 9 , especially NHC 2 H 4 OH, N(C 2 H 4 OH,) 2 , morpholino, NH(C 1-6 -alkyl), NH-(CH 2 ) 2 CO 2 H, NHCH 2 C 6 H 4 CO 2 H, mono- or di-carboxyanilino, NHC 6 H 4 SO 3 H or NHCH 2 SO 3 H.
- R 1 , R 2 , R 3 and R 4 are preferably independently selected from H, C 1-4 -alkyl and C 1-4 -alkyl substituted by OH.
- R 7 , R 8 and R 9 are preferably independently selected from H, C 1-18 -alkyl, substituted C 1-18 -alkyl, C 3-18 -alkenyl, phenyl, substituted phenyl, (CH 2 ) 1-4 -phenyl, substituted (CH 2 ) 1-4 -phenyl, more preferably H, allyl, C 1-18 -alkyl, benzyl, hydroxy C 1-4 -alkyl especially H, methyl, ethyl and 2-hydroxyethyl.
- R 7 , R 8 and R 9 are preferably independently selected from --OH, --SO 3 H and --COOH, especially --OH.
- R 8 and R 9 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring they preferably form a morpholine, piperazine or piperidine ring.
- the identity of the divalent organic linking group L is not critical providing it does not interfere with the performance of the compound.
- divalent organic linking groups represented by L there may be mentioned:
- divalent aliphatic radicals preferably those containing from 2 to 6 carbon atoms, especially C 2-6 -alkylene such as ethylene, trimethylene, propylene, tetramethylene, alpha:beta-dimethylethylene and hexamethylene radicals;
- divalent monocyclic or fused polycyclic aromatic radicals for example optionally substituted phenylene, naphthylene, anthraquinonylene or fluorenylene, such as
- divalent radicals wherein the terminal bonds are attached to carbon atoms of two phenyl or naphthalene nuclei which are joined together either through a direct link or through an atom or chain of atoms which my form a homocyclic or heterocyclic ring.
- nuclear substituted derivatives of the above for example, containing COOH, methyl, nitro and/or sulphonic acid and/or chlorine atoms as substituents in the phenyl or naphthalene nuclei.
- the group NR 2 LNR 3 can be piperazino in which the two ring nitrogen atoms are bonded to the groups represented by X.
- the present invention relates not only to compounds of Formula (1) but also to the salts thereof, especially the alkali metal, ammonium or substituted ammonium salt, particularly the substituted ammonium salt formed with an amine which is volatile at room temperature.
- Preferred volatile amines have a vapour pressure of less than 60 mm Hg, more preferably less than 20 mm Hg, at 20° C. and atmospheric pressure. Examples of preferred volatile amines include methylamine, dimethylamine, diethylamine, methylethylamine, propylamine and isopropylamine.
- Preferred alkali metal salts are the sodium, potassium and Lithium salts, and mixtures thereof with NH 4 + .
- the substituted ammonium salt may contain a cation of the formula + NQ 4 in which each Q independently is an organic radical, or two or three Qs together with the nitrogen atom to which they are attached form a heterocyclic ring and all remaining Qs are selected from C 1-4 -alkyl.
- Preferred organic radicals represented by Q are C 1-4 -alkyl radicals, especially methyl radicals.
- Preferred heterocyclic rings formed by NQ 4 are 5 or 6 membered heterocyclic rings.
- substituted ammonium cations of formula + NQ 4 there may be mentioned N + (CH 3 ) 4 , N + (CH 2 CH 3 ) 4 , N-methyl pyridinium, N,N-dimethyl piperidinium and N,N-dimethyl morpholinium.
- the substituted ammonium salt contains a cation of the formula + NHG 3 wherein each G independently is H or C 1-4 -alkyl provided at least one G is C 1-4 -alkyl, or two or three groups represented by G together with the nitrogen atom to which they are attached form a 5 or 6 membered ring, especially a pyridine, piperidine or morpholine ring.
- the substituted ammonium cation is derived from an amine which is volatile under ambient conditions, i.e. at 20° C. and atmospheric pressure.
- substituted ammonium cations of formula + NHG 3 there may be mentioned (CH 3 ) 3 N + H, (CH 3 ) 2 N + H 2 , H 2 N + (CH 3 )(CH 2 CH 3 ), CH 3 N + H 3 , CH 3 CH 2 N + H 3 , H 2 N + (CH 2 CH 3 ) 2 , CH 3 CH 2 CH 2 N + H 3 , CH 3 CH 2 CH 2 N + H 3 , (CH 3 ) 2 CHN + H 3 , isopropylammonium, pyridinium, piperidinium and morpholinium.
- step (i) diazotisation of amines of the formulae ArNH 2 and Ar 1 NH 2 with a diazotising agent such as HNO 2 , in the cold and preferably below 5° C. to give the corresponding diazonium salts; (ii) coupling the diazonium salt formed from ArNH 2 with an amine of formula H--J--NR 1 H, and coupling the diazonium salt formed from Ar 1 NH 2 with an amine of formula H--J 1 --NR 4 H to give monoazo amines; (iii) reacting the monoazo amines of step (ii) in either order or simultaneously with a compound of formula Cl--X--(NR 2 --L--NR 3 --X) n --Cl, preferably in the presence of base;
- Ar, Ar 1 , X, R 1 to R 4 , J, J 1 , L and n are as defined above unless stated otherwise.
- step (iii) my be followed except that in the definition of X above, instead of the substituent Z there is Cl, and the product of step (iii) is reacted with a compound of formula ZH (wherein Z is as hereinbefore defined) to give a compound of Formula (1).
- the ink preferably contains less than 5%, more preferably less than 2%, especially less than 1% inorganic salts, e.g. NaCl, KCl and NaNO 3 , in order to improve solubility of the dye and reduce the tendency to deposition of solids in the jets of an ink jet printer.
- Inorganic salt content may be lowered to a desired level using a membrane separation process, for example by dialysis of a crude dye in visking tubing or by reverse osmosis.
- the compound of Formula (1) is completely dissolved in the liquid medium to form a solution.
- the ink preferably contains from 0.5% to 20%, more preferably from 0.5% to 15%, and especially from 1% to 5%, by weight of the compound of Formula (1) based on the total weight of the ink.
- the liquid medium is preferably water or an aqueous medium comprising a mixture of water and one or more water-soluble organic solvents, preferably in a weight ratio of water to the solvent(s) from 99:1 to 1:99, more preferably from 95:5 to 50:50 and especially from 90:10 to 60:40.
- Each water-soluble organic solvent is preferably a C 1-4 -alkanol such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol or isobutanol; an amide such as dimethylformamide or dimethylacetamide; an ester such as diacetine; a ketone or ketoalcohol such as acetonemethylethylketone, methylisobutyl ketone or diacetone alcohol; an ether such as tetrahydrofuran or dioxane; a polyalkylene glycol such as polyethylene glycol or polypropylene glycol preferably having molecular weights up to 1000 and especially from 100 to 500; an alkylene glycol containing 2 to 6 carbon atoms such as ethylene glycol, propylene glycol, butylene glycol or triethylene glycol; hexylene glycol or diethylene glycol and thiog
- Preferred water-soluble organic solvents are selected from heterocyclic ketones, especially 2-pyrrolidone and N-methylpyrrolidone; alkylene glycols or lower alkyl ethers of polyhydric alcohols especially ethylene glycol, diethylene glycol and triethylene glycol and especially 2-methoxy-2-ethoxy-2-ethoxyethanol; and polyethylene glycols having a molecular weight of up to 500.
- a preferred specific solvent mixture is a binary mixture of water and either diethylene glycol, 2-pyrrolidone or N-methylpyrrolidone in a weight ratio as mentioned above.
- the ink my contain more than one compounds of Formula (1), for example two or three such compounds.
- the inks of the present invention further comprise one or more of (a) a penetrant to assist permeation of the dye into a paper substrate, (b) a kogation-reducing agent to prevent or reduce the build-up of residue (koga) on the resistor surface in thermal ink jet printers and (c) a buffer such as sodium borate, to stabilise the pH of the ink.
- a penetrant to assist permeation of the dye into a paper substrate
- a kogation-reducing agent to prevent or reduce the build-up of residue (koga) on the resistor surface in thermal ink jet printers
- a buffer such as sodium borate
- the kogation-reducing agent is preferably an oxo anion, such as described in EP 425150A.
- the oxo-anion may be C 2 O 4 2- , SO 3 2- , SO 4 2- , molybdate, AsO 4 3- or more preferably a phosphate ester, a diorganophosphate or more especially a phosphate salt which is particularly effective in reducing kogation.
- phosphate salts there my be mentioned dibasic phosphate (HPO 4 2- ) monobasic phosphates (H 2 PO 4- ) and polyphosphates (P 2 O 7 4- ).
- the selection of counter ion is not believed to be critical and examples include alkali metals, ammonium and alkylammonium cations.
- the kogation-reducing agent is preferably present in the ink at a concentration from 0.001% to 15%, based on oxo-anion, and more preferably from 0.01% to 1% (by weight).
- a further aspect of the present invention provides a process for printing a substrate with an ink using an ink jet printer, characterised in that the ink is as hereinbefore defined.
- a suitable process for the application of an ink as hereinbefore defined comprises forming the ink into small droplets by ejection from a reservoir through a jet so that the droplets of ink are directed at a substrate.
- This process is commonly referred to as ink jet printing, and the ink jet printing processes for the present inks are preferably piezoelectric ink jet printing, and more especially thermal ink jet printing.
- thermal ink jet printing programmed pulses of heat are applied to the ink by means of a resistor, adjacent to the jet during relative movement between the substrate and the jet.
- a preferred substrate is an overhead projector slide or a cellulosic substrate, especially plain paper, which my have an acid, alkaline or neutral character.
- the preferred ink used in the process is as hereinbefore described.
- 5-aminoisophthalic acid (36.2 g) was stirred in water (1 liter) and the pH adjusted to 8-9 by addition of 2N sodium hydroxide.
- Sodium nitrite 14 g was added and the solution added to a mixture of concentrated hydrochloric acid (60 ml) and water (500 ml) at 0°-10° C. After 1 hour at 0°-10° C. the excess nitrous acid was removed by addition of a little sulphamic acid, to give a diazo suspension.
- m-toluidine (21.4 g) was added to water (500 ml) and concentrated hydrochloric acid (25 ml) added. The solution was added over 1/2 hour to the above diazo suspension at 0°-10° C. The pH was adjusted to 4.0 by addition of 47% sodium hydroxide solution and the mixture stirred for 18 hours at 0°-10° C. The pH was adjusted to 8.0 with 47% sodium hydroxide solution, screened and then warmed to 60° C. It was slowly acidified to pH 4.0 with concentrated hydrochloric acid and the product filtered, washed with water and dried to give a monoazo compound.
- inks containing the title dye may be prepared according to the following formulations shown in Table I and Table II wherein figures denote parts by weight for each stated component:
- NMP N-methyl pyrollidone
- MIBK methylisobutyl ketone
- TBT Tertiary butanol
- 5-Aminoisophthalic acid (9.05 g) was stirred in water (150 ml) and the pH adjusted to 8-9 by addition of 2N sodium hydroxide solution.
- 2N Sodium nitrite 25 ml was added and the solution added to a mixture of concentrated hydrochloric acid (25 ml) and water (200 ml) at 0°-5° C. After 2 hours the excess nitrous acid was removed by addition of a little sulphamic acid, to give a solution of diazonium salt.
- the product was then added to water (150 ml) and the pH adjusted to 9.0 with sodium hydroxide solution.
- the solution was added to a mixture of concentrated hydrochloric acid (20 ml) and water (200 ml) to precipitate the title compound in free acid form.
- the title compound was filtered off and converted to the ammonium salt by adding to water (250 ml) and adjusting the pH to 9.0 by addition of concentrated ammonium hydroxide.
- the title compound my be made into an ink by dissolving 2 parts in water:2-pyrollidone (90:10) and adding 0.2 parts of sodium borate.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 2 In place of the 10 g of 2-aminoethanol used in Example 1 there was used 17.2 g of diethanolamine.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 2 In place of the 10 g of 2-aminoethanol used in Example 1 there was used 6.5 g of sodium hydroxide.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Aniline w-methane sulphonate 70 g was added to water (400 ml) to dissolve. The solution was added to the above diazo suspension at 0°-10° C. and pH 7. The mixture was then stirred for 18 hours at 20° C.
- the product was salted to 20% using sodium chloride, stirred for 2 hours, acidified to pH 4 with concentrated hydrochloric acid and then filtered.
- the paste was added to a mixture of water (2 1) and sodium hydroxide (80 g) and heated at 70°-80° C. for 3 hours. It was cooled to 20° C. and salted to 20% using sodium chloride and acidified to pH 3 using concentrated hydrochloric acid. The product was filtered and dried to give the monoazo compound.
- ammonium salt of the title compound when made into an ink by dissolving 3 parts in water:diethyleneglycol:propane-1,2-diol (80:10:10) and printed onto plain paper using a thermal ink jet printing machine gives bright yellow shades with very good water fastness.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated potassium phosphate (0.9 parts) may be added to each of these inks to improve their properties.
- Example 8 In place of the 10 g of 2-aminoethanol used in Example 8 there was used 15.75 g of diethanolamine.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 8 In place of the 10 g of 2-aminoethanol used in Example 8 there was used 14.3 g of morpholine.
- 5-Aminoisophthalic acid was diazotised and coupled onto 1-(2-aminoethyl)-6-hydroxy,4,methylpyrid-2-one as in Example 2. It was then condensed with one equivalent of cyanuric chloride as in Example 2. A further equivalent of monoazo compound was then added, the temperature raised to 45° C. and the pH maintained at 7-8 for 4 hours.
- the reaction mixture was cooled to 20° C. and the pH adjusted to 5 with concentrated hydrochloric acid.
- the product was filtered and reslurried in water (150 ml) and the pH adjusted to 9.0 with sodium hydroxide solution.
- the solution was added to a mixture of water (200 ml) and concentrated hydrochloric acid (20 ml) to precipitate the title compound in free acid form.
- the solution was dialysed to remove chloride tons, screened and evaporated.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 8 In place of the 10 g of 2-aminoethanol used in Example 8 there are used 14.6 g of 2-(ethylamino)ethanol.
- Example 8 In place of the 10 g of 2-aminoethanol used in Example 8 there was used 12 g of n-butylamine.
- Example 8 In place of the 10 g of 2-aminoethanol used in Example 8 there was used 16.6 g of n-hexylamine.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 8 In place of the 10 g of 2-aminoethanol used in Example 8 there was used 19.2 g of 6-amino-1-hexanol.
- Example 8 In place of the 70 g of aniline-w-methane sulphonate used in Example 8 there was used 81.2 g of o-anisidine-w-methane sulphonate.
- Example 17 In place of the 10 g of 2-aminoethanol used in Example 17 there was used 14.3 g of morpholine.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- the monoazo compound made by coupling diazotised 5-aminoisophthalic acid with m-toluidine was prepared as in Example 1. 22.4 g of this monoazo compound was added to water (450 ml) and the pH adjusted to 8.0 by addition of 47% sodium hydroxide solution. It was cooled to 0°-10° C. and a solution of cyanuric chloride (15 g) in acetone (150 ml) added maintaining the pH at 7-8 and a temperature of 0°-10° C. After 3 hours a solution of p-phenylenediamine (3.24 g) in acetone (30 ml) was added and the reaction mixture stirred at 25° C. and pH 7-8 for 18 hours. The reaction mixture was acidified to pH 5 with 2N hydrochloric acid and the product filtered off and pulled dry.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 19 In place of the 22.4 g of the monoazo compound used in Example 19 there was used 21.4 g of the monoazo compound made b 7 coupling diazotised 5-aminoisophthalic acid with aniline- -methane sulphonate followed by removal of the -methane sulphonate group as prepared in Example 8. When made into an ink and printed onto plain paper using a thermal ink-jet printing machine it gave bright yellow shades with very good water fastness.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 10 In place of the 5-aminoisophthalic acid used in Example 10 there is used an equal amount of 4-aminophthalic acid.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 10 In place of the 5-aminoisophthalic acid used in Example 10 there is used an equal amount of 2-aminoterephthalic acid.
- the ammonium salt of the title compound when made into an ink in water and printed onto plain paper using a thermal ink-jet printing machine gives bright yellow shades having very good water fastness.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- 3-Aminobenzoic acid (13.7 g) is stirred in water (250 ml) and the pH adjusted to 8-9 by addition of sodium hydroxide solution.
- Sodium nitrite (6.9 g) is added and the solution added to a mixture of concentrated hydrochloric acid (20 ml) and water (100 ml) at 0°-10° C. After 1 hour at 0°-10° C., the excess nitrous acid is removed by addition of a little sulphamic acid.
- Aniline w-methane sulphonate (21 g) is added to water (150 ml) to dissolve.
- the solution is added to the above diazo solution at 0°-10° C. and pH 7.
- the mixture is stirred at 20° C. for 18 hours.
- the product is salted to 20% using sodium chloride, stirred 1 hour and acidified to pH 4 with concentrated hydrochloric acid and then filtered.
- the paste is added to a mixture of water (700 ml) and sodium hydroxide (40 g) and heated at 70°-80° C. for 3 hours. It is cooled to 20° C. and salted to 20% using sodium chloride and acidified to pH 3 using concentrated hydrochloric acid. The product is filtered and dried to give the monoazo compound (A).
- 5-aminoisophthalic acid is diazotised and coupled onto aniline-methane sulphonate as in Example 8. It is then heated with aqueous sodium hydroxide to remove the -methane sulphonate group as in Example 8 and 7.62 g (1 equivalent) of this product condensed with cyanuric chloride as described in Example 8. After 1 hour, 6.5 g (1 equivalent) of the above monoazo compound (A) in water (500 ml) is added. The pH is adjusted to 8 and the reaction mixture stirred at 25°-30° C. for 18 hours. The pH is adjusted to 5.0 with concentrated hydrochloric acid and the product filtered.
- the product is added to water (500 g) and morpholine (14.3 g) added and the mixture warmed to 80° C. After stirring at 80° C. for 4 hours, the mixture is salted to 30% with ammonium chloride and then cooled to 20° C. and filtered.
- ammonium salt when made into an ink and printed onto plain paper using a thermal ink jet printer gives bright yellow shades with very good water fastness.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- 2-Amino-5-sulphobenzoic acid (21.7 g) was added to a mixture of water (300 ml) and concentrated hydrochloric acid (30 ml) and the mixture cooled to 0°-10° C.
- a solution of sodium nitrite (7.0 g) in water (50 ml) was added dropwise and the mixture stirred at 0°-10° C. for 1 hour.
- the slight excess of nitrous acid was removed with sulphamic acid and then the mixture added slowly to a solution of m-toluidine (10.7 g) in water (200 ml) and concentrated hydrochloric acid (12.5 ml) at 0°-10° C.
- the pH was adjusted to 4.0 and the mixture stirred for 18 hours at 0°-10° C.
- the monoazo compound was filtered off and dried.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 28 In place of the 6.7 g of the monoazo compound derived from 2-amino-5-sulphobenzoic acid and m-toluidine used in Example 28 there is used 5.7 g of the monoazo compound from 5-aminoisophthalic acid and aniline as prepared in Example 8 and in place of the 8 g of 2-aminoethanol there is used 11 g of morpholine.
- the ammonium salt of the title compound when made into an ink and printed onto plain paper using a thermal ink jet printing machine gives bright yellow shades with very good water fastness.
- Example 22 In place of the 3.24 g of p-phenylenediamine used in Example 22 there is used 4.6 g of 2,5-diaminobenzoic acid and in place of the 27.6 g of 2-aminoethanol there is used 39.3 g of morpholine.
- ammonium salt of the title compound when made into an ink and printed onto plain paper using a thermal ink-jet printing machine gives bright yellow shades having high water fastness.
- Example 2 In place of the 10 g of 2-aminoethanol used in Example 1 there is used 10 g of 4-(aminomethyl)benzoic acid.
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 10 The method of Example 10 my be repeated except that in place of adjusting the pH to 9.0 with concentrated ammonia there is used 40% aqueous dimethylamine solution to give the compound of Example 10 in the form of its dimethylammonium salt.
- An ink my be prepared by dissolving 2 parts of the product in 100 parts of water/diethyleneglycol (92.5:7.5).
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 8 The method of Example 8 may be repeated except that in place of adjusting the pH to 9 with concentrated ammonia there is used 40% aqueous dimethylamine solution to give the compound of Example 8 in the form of its dimethylammonium salt.
- An ink my be prepared by dissolving 2 parts of the product in 100 parts of water/diethylene glycol (92.5/7.5).
- Example 15 may be repeated except that in place of adjusting the pH to 9 with concentrated ammonia there is used 40% aqueous dimethylamine solution to give the compound of Example 15 in the form of its dimethylammonium salt.
- An ink my be prepared by dissolving 2 parts of the product in 100 parts of water/diethylene glycol (90/10).
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 6 The method of Example 6 may be repeated except that in place of adjusting the pH to 9 with concentrated ammonia there is used 40% aqueous dimethylamine solution to give the compound of Example 6 in the form of its dimethylammonium salt.
- An ink may be prepared by dissolving 2 parts of the product in 100 parts of water/diethylene glycol (92.5/7.5).
- Example 1 The method of Example 1 my be repeated except that in place of adjusting the pH to 9 with concentrated ammonia there is used 40% aqueous dimethylamine solution to give the compound of Example 1 in the form of its dimethylamine salt.
- An ink my be prepared by dissolving2 parts of the product in water/diethylene glycol (92.5/7.5).
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 6 The method of Example 6 may be repeated except that in place adjusting the pH to 9 with concentrated ammonia there is used 40% aqueous dimethylamine solution to give the compound of Example 1 in the form of its dimethylamine salt.
- An ink may be prepared by dissolving 2 parts of the product in water/diethylene glycol (92.5/7.5).
- Example 10 The method of Example 10 my be repeated except that in place of adjusting the pH to 9 with concentrated ammonia there is used diethylamine to give the compound of Example 10 in the form of its diethylamine salt.
- An ink my be prepared by dissolving 2 parts of the product in 100 parts of water/N-methyl-pyrollidone (92.5/7.5).
- inks may be prepared according to the formulations described in Example 1, Tables I and II wherein the title product is used as dye in the amounts indicated.
- Example 1 The method of Example 1 my be repeated except that in place of 2-aminoethanol there may be used an equimolar amount of hexylamine.
- the resultant product my be made into inks according to Tables I and II in Example 1 and printed onto plain paper.
Abstract
Description
______________________________________ 1,3- or 1,4-phenylene 2-nitro-1,4-phenylene 3-sulpho-1,4-phenylene 4-methoxy-1,3-phenylene 4-sulpho-1,3-phenylene 4-nitro-1,3-phenylene 2-carboxy-1,4-phenylene 2-chloro-1,4-phenylene 4-carboxy-1,3-phenylene 3,7-disulpho-1,5-naphthylene 2-methoxy-1,4-phenylene; ______________________________________
______________________________________ diphenyl azobenzene diphenyloxide diphenyloxadiazole diphenylamine benzanilide diphenylsulphide diphenylurea diphenylsulphone 1,2-bis(phenylcarbamyl)ethylene diphenylmethane 1,4-bis-(phenylcarbamyl)butadiene diphenylketone 1,2-bis-(phenylcarbamyl)ethane diphenylethane 1,3-bis-(phenylcarbamyl)propane diphenylethylene 2,4-dianilino-s-triazine; ______________________________________ and
______________________________________ 2-aminoisophthalic acid 3-amino-4-fluorobenzoic acid 4-aminoisophthalic acid 3-amino-5-hydroxybenzoic acid 5-aminoisophthalic acid 3-amino-4-hydroxybenzoic acid 3-aminophthalic acid 3-amino-2-hydroxybenzoic acid 4-aminophthalic acid 2-amino-6-hydroxybenzoic acid 2-aminoterephthalic acid 2-amino-4-nirobenzoic acid 3-aminobenzoic acid 3-amino-5-nitrobenzoic acid 4-aminobenzoic acid 2-nitro-3-aminobenzoic acid anthranilic acid 2-nitro-5-aminobenzoic acid 4-sulphoanthranilic acid 3-nitro-4-aminobenzoic acid 5-sulphoanthranilic acid 3-acetylamino-5-aminobenzoic acid 2-amino-4-chlorobenzoic acid 3-amino-4-methylbenzoic acid 2-amino-5-chlorobenzoic acid 2-amino-3-methylbenzoic acid 3-amino-4-chlorobenzoic acid 3-amino-4-methoxybenzoic acid 5-amino-2-chlorobenzoic acid 3-amino-4-hydroxybenzoic acid 2-amino-5-methylbenzoic acid 4-aminosalicylic acid 2-amino-6-methylbenzoic acid 5-aminosalicylic acid 2-amino-5-bromobenzoic acid 3-amino-2-naphthoic acid 2-n-butoxy-4-aminobenzoic acid 5-amino-2-naphthoic acid 8-amino-2-naphthoic acid ______________________________________
TABLE I __________________________________________________________________________ Ink Dye Na No. Content Water PG DEG NMP DMK NaOH Stearate IPA MEOH 2P MIBK __________________________________________________________________________ 1 2.0 80 5 6 4 5 2 3.0 90 5 5 0.2 3 1.0 85 5 2 2 0.1 5 1 4 2.1 91 8 1 5 3.1 86 5 0.2 4 5 6 1.1 81 9 0.5 0.5 9 7 2.5 60 4 15 3 3 6 10 5 4 8 1.9 70 20 10 9 2.4 75 5 4 5 6 5 10 4.1 80 3 5 2 10 0.3 11 3.2 65 5 4 6 5 4 6 5 12 4.6 96 4 13 0.8 90 5 5 14 1.2 80 2 6 2 5 1 4 15 1.8 80 5 15 16 2.6 84 11 5 17 3.3 80 2 10 2 6 18 1.7 90 7 0.3 3 19 1.5 69 2 20 2 1 3 3 20 1.6 91 4 5 __________________________________________________________________________
TABLE II __________________________________________________________________________ Ink Dye Na No. Content Water PG DEG NMP CET TBT Stearate BDL PHO 2P PI2 __________________________________________________________________________ 21 3.0 80 15 0.2 5 22 2.0 90 5 1.2 5 23 1.5 85 5 5 0.15 5.0 0.2 24 2.5 90 6 4 0.12 25 3.1 82 4 8 0.3 6 26 0.9 85 10 5 0.2 27 1.5 90 5 5 0.3 28 2.9 70 10 4 1 4 11 29 2.2 75 4 10 3 2 6 30 2.6 91 6 3 31 3.2 76 9 7 3.0 0.95 5 32 4.0 78 5 11 6 33 3.3 86 7 7 34 1.1 70 5 5 5 0.1 0.2 0.1 5 0.1 5 5 __________________________________________________________________________
Claims (17)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/983,170 US5374301A (en) | 1990-07-26 | 1992-11-30 | Inks suitable for use in ink jet printing |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB909016448A GB9016448D0 (en) | 1990-07-26 | 1990-07-26 | Anionic compounds |
GB9016448 | 1990-07-26 | ||
US07723323 US5268459B1 (en) | 1990-07-26 | 1991-06-28 | Azo dyes suitable for ink jet printing |
GB929217963A GB9217963D0 (en) | 1992-08-24 | 1992-08-24 | Inks |
GB9217963 | 1992-09-24 | ||
US07/983,170 US5374301A (en) | 1990-07-26 | 1992-11-30 | Inks suitable for use in ink jet printing |
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US07723323 Continuation-In-Part US5268459B1 (en) | 1990-07-26 | 1991-06-28 | Azo dyes suitable for ink jet printing |
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US5374301A true US5374301A (en) | 1994-12-20 |
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US07/983,170 Expired - Lifetime US5374301A (en) | 1990-07-26 | 1992-11-30 | Inks suitable for use in ink jet printing |
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